JP2008516922A5 - - Google Patents
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- Publication number
- JP2008516922A5 JP2008516922A5 JP2007536122A JP2007536122A JP2008516922A5 JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5 JP 2007536122 A JP2007536122 A JP 2007536122A JP 2007536122 A JP2007536122 A JP 2007536122A JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- pyrrolidinyl
- phenyl
- methylethyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NNPOKMDCSQIRDT-HXUWFJFHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-HXUWFJFHSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-GOSISDBHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-GOSISDBHSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-LJQANCHMSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-LJQANCHMSA-N 0.000 claims 1
- YAORFRUOVGBQJQ-OAHLLOKOSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-OAHLLOKOSA-N 0.000 claims 1
- NNPOKMDCSQIRDT-FQEVSTJZSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-FQEVSTJZSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-SFHVURJKSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-SFHVURJKSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-IBGZPJMESA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-IBGZPJMESA-N 0.000 claims 1
- YAORFRUOVGBQJQ-HNNXBMFYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-HNNXBMFYSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-GOSISDBHSA-N (4-cyclobutylpiperazin-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-GOSISDBHSA-N 0.000 claims 1
- WDARRXDQPULKMV-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C(=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)F)=N1 WDARRXDQPULKMV-INIZCTEOSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-SFHVURJKSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-SFHVURJKSA-N 0.000 claims 1
- OLXZIKGIGJIHLH-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 OLXZIKGIGJIHLH-INIZCTEOSA-N 0.000 claims 1
- JTACQVQJYZNHKP-AWEZNQCLSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC2)C2CCC2)CC1 JTACQVQJYZNHKP-AWEZNQCLSA-N 0.000 claims 1
- PKXKZAADEFDOIS-KRWDZBQOSA-N (4-ethylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PKXKZAADEFDOIS-KRWDZBQOSA-N 0.000 claims 1
- GWARTCUETWOJMY-HNNXBMFYSA-N (4-pentan-3-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 GWARTCUETWOJMY-HNNXBMFYSA-N 0.000 claims 1
- RMJUTJDMAVAABO-HNNXBMFYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 RMJUTJDMAVAABO-HNNXBMFYSA-N 0.000 claims 1
- HRZIINBMVJNVJE-IBGZPJMESA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-(4-pyrrol-1-ylphenyl)pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=CC=C2)CC1 HRZIINBMVJNVJE-IBGZPJMESA-N 0.000 claims 1
- VJZWGYSVNQTUQK-ZDUSSCGKSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[2-(trifluoromethyl)pyrimidin-5-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=NC=2)C(F)(F)F)CC1 VJZWGYSVNQTUQK-ZDUSSCGKSA-N 0.000 claims 1
- YOJAJLNNCCLRHB-AWEZNQCLSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 YOJAJLNNCCLRHB-AWEZNQCLSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- VYPBIEFMFRZIFJ-LJQANCHMSA-N 1-[4-[(3r)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-LJQANCHMSA-N 0.000 claims 1
- VYPBIEFMFRZIFJ-IBGZPJMESA-N 1-[4-[(3s)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-IBGZPJMESA-N 0.000 claims 1
- URKJTOVLGKEWAE-IBGZPJMESA-N 1-[4-[(3s)-3-(4-pentan-3-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 URKJTOVLGKEWAE-IBGZPJMESA-N 0.000 claims 1
- UPMCRBZHCZHCPO-IBGZPJMESA-N 1-[4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 UPMCRBZHCZHCPO-IBGZPJMESA-N 0.000 claims 1
- AFTLCCALAJJJBT-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 AFTLCCALAJJJBT-SFHVURJKSA-N 0.000 claims 1
- PUKCWLYBBDPLFO-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]pyrrolidin-2-one Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(CCC2)=O)CC1 PUKCWLYBBDPLFO-SFHVURJKSA-N 0.000 claims 1
- QVWXADQLHGQINK-LPHOPBHVSA-N 1-[4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 QVWXADQLHGQINK-LPHOPBHVSA-N 0.000 claims 1
- NRDUEPBCTYCHEB-FQEVSTJZSA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)-1,4-diazepane-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CCC2)CC1 NRDUEPBCTYCHEB-FQEVSTJZSA-N 0.000 claims 1
- KJDLVOPRILNRCJ-IBGZPJMESA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)piperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 KJDLVOPRILNRCJ-IBGZPJMESA-N 0.000 claims 1
- DXWBJTZKDPMYNH-KRWDZBQOSA-N 3-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C#N)CC1 DXWBJTZKDPMYNH-KRWDZBQOSA-N 0.000 claims 1
- ADUVQOLQHWNHBQ-SFHVURJKSA-N 4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 ADUVQOLQHWNHBQ-SFHVURJKSA-N 0.000 claims 1
- UCHKYAUOAIHHNW-KRWDZBQOSA-N 4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 UCHKYAUOAIHHNW-KRWDZBQOSA-N 0.000 claims 1
- IVFJQUPDJYGNPR-WMZOPIPTSA-N 4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]benzonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 IVFJQUPDJYGNPR-WMZOPIPTSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QBJWLJXVGOFHFX-GOSISDBHSA-N [(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-GOSISDBHSA-N 0.000 claims 1
- QIPODOWWZRVEKL-SFHVURJKSA-N [(3s)-1-(4-imidazol-1-ylphenyl)pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=NC=C2)CC1 QIPODOWWZRVEKL-SFHVURJKSA-N 0.000 claims 1
- ZYBCHPBYMVPNQH-KRWDZBQOSA-N [(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C(=CC(=CC=2)C=2ON=C(C)N=2)F)CC1 ZYBCHPBYMVPNQH-KRWDZBQOSA-N 0.000 claims 1
- JLXVJQQSMXXOCY-SFHVURJKSA-N [(3s)-1-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C=2ON=C(C)N=2)CC1 JLXVJQQSMXXOCY-SFHVURJKSA-N 0.000 claims 1
- UYBOKBHVPBWUFH-KRWDZBQOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 UYBOKBHVPBWUFH-KRWDZBQOSA-N 0.000 claims 1
- CBCAEUGHISGMJQ-INIZCTEOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 CBCAEUGHISGMJQ-INIZCTEOSA-N 0.000 claims 1
- VBSGTTPSUKPZJQ-SFHVURJKSA-N [(3s)-1-[4-(1,2-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=CC=2)CC1 VBSGTTPSUKPZJQ-SFHVURJKSA-N 0.000 claims 1
- BKPMNQNQXRJZKV-SFHVURJKSA-N [(3s)-1-[4-(1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC=NC=2)CC1 BKPMNQNQXRJZKV-SFHVURJKSA-N 0.000 claims 1
- VGBIKTCJQQKEFX-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-4-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)OC=2)CC1 VGBIKTCJQQKEFX-IBGZPJMESA-N 0.000 claims 1
- UBRPQLXMDZVHCP-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NC=2)CC1 UBRPQLXMDZVHCP-IBGZPJMESA-N 0.000 claims 1
- PCEWCRUEPDUGSU-IBGZPJMESA-N [(3s)-1-[4-(2-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(=NC=C2)C)CC1 PCEWCRUEPDUGSU-IBGZPJMESA-N 0.000 claims 1
- YYNFVEZVQLHDGC-IBGZPJMESA-N [(3s)-1-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CCC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C(C)C)=N1 YYNFVEZVQLHDGC-IBGZPJMESA-N 0.000 claims 1
- PATUCRXRMASYJU-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PATUCRXRMASYJU-IBGZPJMESA-N 0.000 claims 1
- WHCWUQZKDPMIGH-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 WHCWUQZKDPMIGH-IBGZPJMESA-N 0.000 claims 1
- QBJWLJXVGOFHFX-SFHVURJKSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-SFHVURJKSA-N 0.000 claims 1
- CQFSDSNLSQURSR-LPHOPBHVSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-[(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 CQFSDSNLSQURSR-LPHOPBHVSA-N 0.000 claims 1
- PXVPPTFSYIKJBE-IBGZPJMESA-N [(3s)-1-[4-(4-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=C(C)N=C2)CC1 PXVPPTFSYIKJBE-IBGZPJMESA-N 0.000 claims 1
- NIXPOQHPJVUNEI-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)ON=2)CC1 NIXPOQHPJVUNEI-SFHVURJKSA-N 0.000 claims 1
- AWSWXQJSGZQQOU-IBGZPJMESA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 AWSWXQJSGZQQOU-IBGZPJMESA-N 0.000 claims 1
- RHMDXLFQFOBXOH-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 RHMDXLFQFOBXOH-SFHVURJKSA-N 0.000 claims 1
- IGSLFRDFOPKRTK-QFIPXVFZSA-N [(3s)-1-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)CC1 IGSLFRDFOPKRTK-QFIPXVFZSA-N 0.000 claims 1
- OJDIWUZFITXDRO-INIZCTEOSA-N [(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C=2ON=C(C)N=2)CC1 OJDIWUZFITXDRO-INIZCTEOSA-N 0.000 claims 1
- MSKUPINGSAZGTP-GJZGRUSLSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 MSKUPINGSAZGTP-GJZGRUSLSA-N 0.000 claims 1
- QPDUYTMJXPZQDA-FQEVSTJZSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 QPDUYTMJXPZQDA-FQEVSTJZSA-N 0.000 claims 1
- HTSWAPRVWBKBGO-SFHVURJKSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 HTSWAPRVWBKBGO-SFHVURJKSA-N 0.000 claims 1
- LXKMZMNNAKJQFD-IBGZPJMESA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 LXKMZMNNAKJQFD-IBGZPJMESA-N 0.000 claims 1
- QEZZAHLGBVDWNB-KRWDZBQOSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 QEZZAHLGBVDWNB-KRWDZBQOSA-N 0.000 claims 1
- GKAQOFAZTNGKLA-HNNXBMFYSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 GKAQOFAZTNGKLA-HNNXBMFYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005533 aryl carboxamido group Chemical group 0.000 claims 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| GB0508441A GB0508441D0 (en) | 2004-10-15 | 2005-04-26 | Novel compounds |
| PCT/EP2005/011371 WO2006040192A1 (en) | 2004-10-15 | 2005-10-13 | Pyrrolidine derivatives as histamine receptors ligands |
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| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| CA2655604C (en) | 2006-06-23 | 2016-08-09 | Abbott Laboratories | Cyclopropyl amine derivatives |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| CN101835750B (zh) | 2007-08-22 | 2013-07-17 | 阿斯利康(瑞典)有限公司 | 环丙基酰胺衍生物 |
| US20090170869A1 (en) | 2007-09-06 | 2009-07-02 | Desmond John Best | Piperazine derivative having affinity for the histamine h3 receptor |
| AU2009216851B2 (en) | 2008-02-22 | 2013-11-07 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| CA2721303C (en) | 2008-05-08 | 2016-06-28 | Evotec Ag | Azetidines and cyclobutanes as histamine h3 receptor antagonists |
| US8236792B2 (en) | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| CA2731897C (en) * | 2008-08-06 | 2013-07-02 | Pfizer Limited | Diazepine and diazocane compounds as mc4 agonists |
| WO2010040661A1 (en) | 2008-10-09 | 2010-04-15 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| AU2009312856A1 (en) | 2008-11-10 | 2010-05-14 | F. Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
| CA2751239C (en) | 2009-02-02 | 2016-11-01 | Adam James Davenport | Azetidines as histamine h3 receptor antagonists |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2011016559A1 (ja) * | 2009-08-07 | 2011-02-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| US20110201623A1 (en) | 2010-02-18 | 2011-08-18 | Uczynski Michael A | Crystalline Form Of A Cyclopropyl Benzamide Derivative |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| WO2020163689A1 (en) | 2019-02-08 | 2020-08-13 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | 20-hete formation inhibitors |
| JP7820560B2 (ja) * | 2022-03-31 | 2026-02-25 | 廣州必貝特醫藥股▲ふん▼有限公司 | １，４－ジヘテロシクリル置換芳香環若しくは芳香族複素環系化合物及びその使用 |
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| US6093718A (en) * | 1996-08-14 | 2000-07-25 | Zeneca Limited | Substituted pyrimidine derivatives and their pharmaceutical use |
| DE10034338C2 (de) * | 2000-07-14 | 2002-06-20 | Forschungszentrum Juelich Gmbh | Mehrpoliges kaskadierendes Quardrupel-Bandpaßfilter auf der Basis dielektrischer Dual-Mode-Resonatoren |
| WO2003062234A1 (en) * | 2002-01-23 | 2003-07-31 | Yamanouchi Pharmaceutical Co., Ltd. | Quinoxaline compounds |
| EP1556046A1 (en) * | 2002-10-23 | 2005-07-27 | Janssen Pharmaceutica N.V. | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
| MXPA05011352A (es) * | 2003-04-23 | 2005-11-28 | Glaxo Group Ltd | Derivados de piperazina y su uso para el tratamiento de enfermedades neurologicas y psiquiatricas. |
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2005
- 2005-10-13 WO PCT/EP2005/011371 patent/WO2006040192A1/en not_active Ceased
- 2005-10-13 US US11/576,968 patent/US20080045506A1/en not_active Abandoned
- 2005-10-13 PL PL05802453T patent/PL1802307T3/pl unknown
- 2005-10-13 SI SI200530241T patent/SI1802307T1/sl unknown
- 2005-10-13 PT PT05802453T patent/PT1802307E/pt unknown
- 2005-10-13 AR ARP050104299A patent/AR051391A1/es unknown
- 2005-10-13 EP EP05802453A patent/EP1802307B1/en not_active Expired - Lifetime
- 2005-10-13 AT AT05802453T patent/ATE387202T1/de not_active IP Right Cessation
- 2005-10-13 DE DE602005005080T patent/DE602005005080T2/de not_active Expired - Lifetime
- 2005-10-13 JP JP2007536122A patent/JP2008516922A/ja not_active Withdrawn
- 2005-10-13 ES ES05802453T patent/ES2303280T3/es not_active Expired - Lifetime
- 2005-10-13 HR HR20080227T patent/HRP20080227T3/xx unknown
- 2005-10-13 DK DK05802453T patent/DK1802307T3/da active